Data Processing and The Psychology of Emerging Adulthood
by CamilleCM
Summary: Chandler Bing graduated from college in 1991, it was time to grow up and face the challenges of adulthood awaiting him. Part II of "A Year In The Life" series — character study one-shots exploring one year in the backstory of each Friend. Canon compliant, pre-show timeline.
1. Part One

Chandler Bing was the only one not having fun.

Maybe he wasn't drunk enough or everybody else in the room was delaying the inevitability of what was coming ahead. How come he couldn't do just that?

Because his best friend was an engaged man and about to go to graduate school.

Because he got into college thinking it would be better than an all-male boarding school, and it turned out it wasn't.

Mostly because, starting from this day, he would go from "Chandler Bing: IT major, Senior" to "Chandler Bing: Unemployed, unmotivated, does absolutely nothing with his life."

College, in many ways, wasn't the experience he hoped for. But he had made some friends, he had a roommate-turned-best friend, he was even in a band. That was still something. It was a safety bubble and now he was losing the semblance of identity he had formed in the last four years.

They were moving on, there was no band anymore, everyone seemed to have a plan.

It had dawned on him in the morning, while he was getting ready for the reception, alone in his mother's empty penthouse―waiting for her to call and announce that she couldn't make it―he was stuck there. Ross was going to get married in the summer and move in with Carol. Ross's sister, who had become one of his best friends, or one of his better friends at least, would have no reason to hang out with him anymore. Gandalf, Howard, Bernie and everyone else at NYU would move on, and there he was. In a house he hated, with nowhere else to go.

He couldn't skip the graduation ceremony, it was mandatory. He had a front-row view of the tossing of caps and hugging of professors, looking at all those smiling faces, happily celebrating with their friends and family beaming with pride. The pompousness of the celebrations made him feel out of step, weirdly dissociated from this whole day, and possibly, he feared, the rest of his days.

Ross's parents were there, of course. He had never seen two parents as proud and happy as the Gellers were. Cheering their son's name, hugging and embracing him, constantly filming and taking pictures of every moment.

He decided to stay for the reception NYU had thrown in honor of the Class of 91'. It was _something to do_, and admittedly, the luncheon had the best shrimp cocktail in the free world.

He found Monica standing by the buffet, picking and choosing meticulously what to put on her plate. He took comfort in the fact he wasn't the only one avoiding the Jubilee of Ross.

About two years earlier, Monica had started to visit Ross at NYU regularly after moving to the City. Chandler could still remember the night he found Monica at the door of their room and let her in with the implicit pact of never bringing up the Toe Incident of 1988, that strange Thanksgiving night at the Gellers that ended one of his most awkward attempts at flirting in him losing the tip of his toe after she accidentally dropped a knife on his foot.

Naturally, none of them had wanted to bring up that memory again, until a guy passed by their dorm and called Chandler 'Sir Limps A Lot', making the conversation inevitable. She had apologized again, without further explanation for her strange behavior on that night, and as compensation, offered to divulge Ross's high school nickname. Chandler, inevitably, jumped on the opportunity, and since then, never failed to bring up the 'Wet Pants Geller' story with his roommate at any given chance.

Over time, they became friends, bonding over Ross's extravagant―and exponentially more ridiculous with time―romantic gestures for Carol and exchanging high-school war stories.

They kept in touch mostly from then on through Ross: Engagement party, birthdays, holidays.

"To life after college." She raised her drink in a toast and Chandler dejectedly clinked his glass with hers. "Wow, you actually manage to be even grumpier at a graduation party," she added.

"I'm not grumpy, I'm realistic. I'm the only one here with no plan. I can already feel the emotional paralysis taking over my body."

"Chandler, everyone here is freaked out and unsure about the future."

He snorted. "Not Ross."

"Ross is an exception."

"You were perfectly happy at your graduation, you had a job lined up and a place to live."

Monica put down her drink and held her hands. "I got lucky, ok? But I was still scared. It's a good kind of scared. You need to relax, maybe go out to celebrate."

"Really? Relaxation lessons from you?" Chandler sneered. "May I remind you, on your graduation day, you went to the discount store and picked up a new set of fitted sheets. You sure know how to celebrate."

"Yeah, but the store was having a kickass sale and the bedding was 75 percent off," Monica said, dreamily reminiscing. "Now, that's my kind of party."

Chandler smiled when a familiar voice hit the air.

"Bing, you're here!"

He turned his head to find Mike "Gandalf" Ganderson, Howie Blum and Bernie Spellman walking towards him. Monica picked up her drink, squeezed his shoulder with a smile and congratulated him before leaving.

"I was looking for you. Are you ready to _partaaaay_?"

Chandler groaned inwardly. He wasn't in the mood. Gandalf's entertainment wizardry only reminded him that the good times of college parties and recklessness were truly over.

"Look, this party is lame, it's for the parents, we'll have another one later on. Come by the bar, and get your passport ready," Gandalf said with a wink before noticing Chandler's distraught expression. "What's with you, man?"

Chandler sighed, rubbing a hand across his neck. "I don't know, I don't feel like partying, it's over, Gandalf. College is over."

"Only if you want it to be."

He looked at Gandalf with narrowed eyes. "I don't think it's up to me."

"Just re-enroll. I'm taking a feminism class, Women's studies. Two words for you: Freshmen. Girls."

Chandler cringed. Sure, he was stuck in life, but he had no intention to be stuck in college forever, like a ghost with unfinished business who couldn't pass onto the next world.

His attention switched to Carol, who joined Ross. He hadn't talked to Ross all day. Sure, it was a special day, his family was here, his fiancée too. And Chandler had neither of those, but he feared this would become the new normal.

Gandalf noticed Chandler staring at the couple. "As you can imagine, I lost quite a lot of friends and girlfriends to graduation. Ross was smart to marry one of them. And you're even smarter not to tie yourself up to anyone. You can hang out again in bars and freshmen girls will throw themselves at you."

Chandler's main preoccupation on graduation day wasn't college parties or freshmen girls, he was on the verge of losing the few friends he had made. Gandalf to college parties, Ross to his fiancée, and by extension, Monica too. She lived in the city but he figured once her brother graduated, she wouldn't have a reason to hang out with him. Chandler always felt his friends were only his friends by convenience. Maybe they liked him, but no one had gone out of their way to be friends with him. Except for Ross, and he would become a married man in a few weeks.

He turned in early, the Gellers had gone home, Gandalf and his party squad were out to celebrate. He entered his mother's townhouse in the Upper East Side, took a beer out the fridge and slumped on the couch. He pushed the button of his answering machine.

"Hey honey, I'm sorry I couldn't be there, but I told Ross to take pictures."

Chandler sighed. He never quite understood the relationship and seeming affection his mother had for his best friend. At first, the fact she took an interest in his circle of friends was a pleasant surprise but now, he was left with a lingering feeling of discomfort anytime she mentioned him.

As alluring as Gandalf's way of life was, graduating from college once in a lifetime was enough.

* * *

Chandler Bing was never a fan of holidays.

It was no secret that Thanksgiving was like a bad practical joke to him. It extended to Christmas, a whole month designed to remind lonely people like him of just how lonely they were. And every other holiday after that, whether a product of religion or corporations, from New Year's Eve to Valentine's Day, seemed to be around shoving onto people's faces the two things that deserted his life: family and love. The mistletoe kisses, the family dinners, the exchange of gifts, the midnight kisses―a series of cruel rituals concocted to taunt him.

But at the very least, he knew what to expect from these holidays.

Summer vacation was different. At first, it came as a relief, the end of a forgettable school year, but it usually never lived up to expectations. For many of his fellow boarding school classmates, summer was like getting out of prison with the promise of sun and girls on the outside. He wasn't particularly fond of the sun, and girls weren't particularly fond of him.

There was something comforting about the cycle of school life. One bad summer, it would be just that. Another one would always come in a few months.

However, the summer after college graduation felt like a bad omen for the rest of his life. There was no new college year to look forward to. Life was now a never-ending bad summer.

The summer of 1991 sure felt like the start of a bad life. Or an empty one, like the empty penthouse he had all to himself for two whole months. He didn't get any news from the college friends that had promised to keep in touch, and he imagined the Gellers to be too caught up in Ross and Carol's wedding planning.

He suspected there were two types of college graduates, the ones that jumped on a new job straight away, and those who had the best summer of their lives―travels, barbecues, beach trips. Then there was him, with no job and no sun. Instead, it was TV specials, frozen pizza, all-nighters on the Super Nintendo, and watching Terminator 2 alone about half a dozen times at the nearest movie theater.

It almost came as a relief when, midway through July, Ross had called him to help him with the move into his and Carol's new apartment. On a warm summer afternoon, he was in the Upper West Side, witnessing Ross awkwardly trying to park a moving truck with Monica giving him instructions.

"You couldn't have invited anyone else? You're expecting me and Monica to move all this stuff?" He told Ross.

"For your information, I got Monica to compensate for you," Ross retorted.

"Thanks, man."

Chandler had envisioned the afternoon to consist of moving a few boxes then sharing some beers with Ross and relax. The moment he saw Monica in overalls with a t-shirt underneath, a logbook and a cap, he realized the words 'hang out' and 'relax' would not be part of that day's vocabulary.

"Ok, let's move. Ross and I will lift boxes and Chandler … You can help unwrap things," Monica ordered.

"Great, I like feeling valued and appreciated," Chandler said with a sullen growl.

"You have two hours, then you can take a break of 6 minutes, use them wisely."

Ross and Chandler shared a look. Monica went to him and tapped his shoulder from behind as he was about to grab the bubble wrap cutter. "Hey, I need your help with my ad for a roommate. I didn't get any calls for mine! It's as if they were giving out rent-controlled apartments for free in this city," she whined.

"Uh oh, what did you write in your ad?"

"I just put in some … requirements," she said coyly.

She handed him the newspaper then pointed a finger to him. "_No_ editorializing."

Chandler nodded with a grin and examined the ad, well aware of Monica's scrutinizing gaze.

"22 years old single professional female," he read out loud, trying not to burst out laughing. "One room available. Rent to be shared equally. Non-smoking, quiet and clean roommate required. Prefers organized systems and common rules. With a stable job. No parties allowed. Doesn't leave dishes in the sink. No pets allowed. Will have to keep the bathroom clean at all times and won't bring suspicious people for intimate relations. Please be clean. Serious inquiries only, please."

He looked at her with wide eyes. "This is insane."

"What? These aren't unreasonable requirements," Monica defended.

"They are, for normal people. Let me rewrite this."

He took her pen and started scribbling while muttering. "_Female professional_," he said looking up at her. "The single thing will only attract creeps," he added and she grimaced. _"Looking for a clean and reasonable roommate_. _No smoking and no pets allowed. Serious inquiries only, please_ … and voilà!" He concluded with triumphant emphasis.

"We'll see," she replied with a pout.

Chandler laughed, he knew he was right, and he knew Monica knew he was right, but she would never admit it and he wasn't going to insist. Just like the aftermath of the Toe Incident, this had been the leitmotiv of their friendship, silent and mutual understandings.

He went to help out Ross, his ex-roommate was opening a box marked as fragile.

Chandler immediately recognized it. His arch-enemy, the object of his nightmares. Ross was dusting an air purifier―no, _the_ air purifier, what Chandler considered to be possibly the most effective sound torture instrument unintentionally invented, he had regretted not selling the idea to the military.

"Ross, you're not keeping the air purifier, are you?" he asked.

"Yes I am, why?" Ross asked back with genuine concern.

"One night with Carol and this monster, and she's going to divorce you. Hell, we weren't married and I wanted to divorce you!" Chandler laughed at his own joke.

"Hey! No divorce jokes before the wedding, it's bad luck. Divorce isn't funny, man!" Ross said in a burst of animosity.

"It can be," he muttered under his breath, avoiding Ross's glare just to meet Monica's. "What if you divorce a clown?" he added, and she smirked, hitting him with the wrap bubble on his chest.

"Keep your little jokes for the best man speech, all right," Ross added. "Speaking of which, what's the plan for the bachelor party?"

Chandler's eyes went wide. "Bachelor party?"

"Well yeah, I'm getting married in two weeks. It's time―oh wait, it was going to be a surprise!"

With a pale face, Chandler looked at Monica who suspected his lack of any bachelor party planning, she nudged him with an elbow to prompt him to answer.

"Oh yeah, you got me … It _was_ going to be a surprise," Chandler said with a plastered smile.

Ross shrieked excitedly, before going downstairs.

"You are so screwed," Monica whispered to him, patting his shoulder, before following her brother.

**…...**

"The hut! The basement of a Pizza Hut!"

"I thought it would be intimate."

"I can't believe you're my best man."

"Hey, you get what you pay for."

"I didn't pay you anything."

"Exactly!"

Ross sighed as Monica and Carol were stifling a laugh, while Chandler was recounting the sad, uneventful bachelor party he had improvised the night before. They were sitting in Monica's apartment. It was the nicest, cleanest, most sophisticated apartment Chandler had ever been in. He was used to fancy houses and apartments, but none of them had the quaint charm of Ross's little sister's place. He wasn't in the least surprised given everything he knew about her.

"What about you, how was your bachelorette party? Did it live up to the Hut?" Ross asked his fiancée while shooting looks at Chandler.

Monica and Carol looked at each other and giggled. "You don't want to know," Monica said as they high-fived.

Chandler shook his head. The Gellers just didn't know how to have fun. He looked back at his best friend. "Look, after the wedding and the honeymoon, let's spend a weekend in Atlantic City, ok? We'll play some poker, go to some bars. A retroactive bachelor party if you will, what do you say?"

"Atlantic City, huh?" Ross pondered. "There's actually a dinosaurs theme park at the convention center, could we―could we go to that?" Ross asked sheepishly.

"The _kids_ convention center?" Chandler looked at Monica who was barely containing her laugh. "Yes, we will do that. Hit some bars, play some poker and check out T-Rexes!"

"Actually, the plural of T-Rex is T-Rex―"

"Okay, buddy."

* * *

Ross and Carol got married by the seaside in Long Island during a summer themed wedding. The Gellers were ecstatic, they had gone all out with a lavish outdoor reception following the ceremony at a nearby church. It had gone seamlessly, Carol was radiant and Ross was nervous but excited like a little kid. Chandler was always intrigued by his best friend's love for love, and a little envious if he was honest. He was getting bored with the only few people he knew at the wedding―Ross's geeky friends from the Paleontology department at NYU―and was relieved when Monica saved him from them.

"I posted your ad and I found a roommate," she announced.

"Told you it would work."

"Yeah, yeah, whatever." She rolled her eyes and he smiled. Monica stared at him for a moment, her eyes moving over his features as if gauging them somehow. "So how was your summer? You kind of disappeared on us."

"Sad. Lonely," Chandler answered.

"The Bing bellyaching party, how could I have missed that?" she said with an amused smirk.

"I can't stand living in that house anymore," he said with earnest despair.

Monica's smile faded, still looking at him. She took a sip out of her drink when suddenly her face lit up. "Hey, the apartment across the hall from mine is up for rent. I actually know the landlord, I could put in a good word for you."

Chandler tapped his chin, contemplating her offer. "Depends. Would I have to see you every day?"

Monica gaped in playful shock and kicked him under the table. "Look, it's a nice place, not as nice as mine―"

"Obviously."

"But for a bachelor like you, it's pretty nice."

"Oh yes, my wild bachelor reputation preceding me," Chandler deadpanned.

"But do you have a job?" she asked seriously. "Or is Mommy giving you pocket money?" she teased him.

"Ha ha. I guess I do need to get a job." Chandler furrowed his eyebrows as if hit by the realization for the first time. "That company I was an intern for wants me back."

"I thought you hated that job."

"I do. But I also hate looking for a job, _and_ living in that house."

"Just tell me if you want to move in." Monica got up, taking her drink with her when she turned back to him. "What do you even do?"

"I would tell you but it would be rude for you to fall asleep at your brother's wedding."

She grinned and Chandler watched as Monica joined her parents and Ross dancing with Carol on the dancefloor. He thought about her offer. He was already spending most of his weekends at her place, hanging out with Ross and Carol after having drinks at Christopher's Pub, the bar downstairs. It was tempting, and he did need to get a job, if only to avoid going crazy, sitting at home alone with his own thoughts.

A job and an apartment, maybe it was time to grow up. Growing up was inevitable but a group of friends across the hall would make it just a little less scary.

* * *

Chandler Bing never quite understood where his talent for math came from.

His mother was a writer, his father loved to sing and dance and perform―and before coming out, divorcing his mother then leaving for Las Vegas with Chandler's 6th-grade teacher to become an entertainer, Charles Bing was a college professor of English literature at Columbia.

His parents were witty, sharp-tongued people, masters of the word, as he witnessed multiple times whenever they had debated, sparred and fought.

It always felt strange that numbers were easy for him. That, of all the talents he could have inherited, he had an aptitude for mathematics from a young age. An innate ability to understand numbers and solve the problems they posed. Before tests, he'd spend the evenings watching Rowan and Martin's Laugh-In on TV and listening to comedy albums on his father's old turntable, and he would still get an A.

Chandler liked easy and hated that he liked easy. He had studied numbers in college because they were easy for him―logical, symmetrical and predictable in the patterns and repetitions they unveiled. And maybe, deep down, it was his own little rebellion. Entertainment and art, it was for crazy, mad people. People like his parents. He'd rather get a job that wouldn't destroy families and holidays.

He had been an intern then a temp for two summers at Dronetec Inc. A sprawling conglomerate with interests ranging from system information to fine foods, and he had liked it enough. They had called him for a job position as a junior data processor which he accepted; it was surprisingly good money and temptingly low stress. Most importantly, it was better than doing nothing. Maybe he would figure out his true passion within a couple of months. For now, a job would allow him to get the apartment in Monica's building.

It was what kept him going when he got bored out of his mind the very first day at his job. After some mind-numbingly boring introduction sessions, sitting at his desk with the spreadsheet software open and feeling terribly useless, typing numbers and data that he felt, made very little difference in anyone's life, he decided to spend the afternoon decorating his desk with as many distractions and toys he sensed were going to be needed in the future.

This job wasn't for him, not for the long term at least. He had to make sure it was temporary, to get his life in order. There was the danger of time slipping away, of squandering whatever potential he had.

He left work to go back to his mother's penthouse. He packed a few bags and headed to the Village, already forgetting about work, and feeling genuine excitement about the prospect of his new apartment.

Greenwich Village, friends, a downstairs bar? For once, the positives in his life were outweighing the negatives.

He picked up the keys from the superintendent―who was having a lively chat with an old man in a robe about pet-owners' rights―and went upstairs.

Opening the door to apartment 19, he immediately felt at home. He left his bags, and was about to knock on apartment 20's door but decided against it.

When Chandler entered his friend's apartment, he was surprised to notice some important changes since the last time he had been there. There were plants everywhere. He was moderately sure Monica wasn't a houseplants aficionado. He spotted her a little flustered, closing quickly the door to the closet by the bathroom door.

"I think I got the wrong address, is this Tarzan's apartment?" he joked, moving closer inside the apartment. "What's with the plants?"

"They're Phoebe's plants," she replied.

"Phoebe?" It took him a couple of seconds to realize Phoebe was the name of the roommate he was yet to meet. "Hum. Veni, vidi, vici," he said as the roommate in question appeared from the other bedroom and without introduction, she looked at him with narrowed eyes.

"Huh?" Phoebe said.

"Latin," Chandler clarified succinctly.

She approached the kitchen area and studied him, plucking at the air in front of him. "No, you're more like a Swedish guy. A goofy Swedish guy. Although, wait―" she suddenly tensed, squinting her eyes. "You look a little like a French guy."

Chandler paled, baffled by what was happening. This woman was at opposite ends of the type of roommate he imagined Monica to pick. She was blonde, tall, wearing a multi-layered bohemian outfit, and just plain weird.

"I'm not saying I'm Latin. It's … never mind. Monica, I need to talk to you."

Monica joined them at the entrance, and she too squinted her eyes at Chandler. "She's right. You do look a little French."

"Et tu, Geller?"

Monica smiled, then turned to Phoebe. "Phoebe, this is Chandler Bing, he's my brother's best friend moving across the hall."

"And your friend."

"Yes, also my friend Chandler."

"French friend Chandler apparently," he muttered.

"Chandler, please," she scolded with gritted teeth. "This is my roommate, Phoebe Buffay."

"Nice to meet you, Latin French friend Chandler Bing. You're a strange one."

"Nice to meet you too," Chandler mumbled, before pulling Monica out of her apartment into the hall. As soon as they entered his apartment, Monica inspected every corner and went into the bedrooms, visibly satisfied. She noticed the bags and small boxes still cluttering the middle of the living room. "You haven't unpacked yet!"

Chandler rolled his eyes as she started to open the boxes and organize their content in the allocated space.

She stopped when she noticed a box wrapped with a ridiculous amount of tape. Without missing a beat, she started to unwrap it.

"Hey!" Chandler pulled himself in front of the box. "This is private. PROPERTY OF CHANDLER BING―see, no one can touch it."

"How fifth grade of you. What's in it?"

"It's private, ok! I―I don't need to explain myself to you."

"Come on, you know it's going to eat me up and I'm not going to give up."

Monica nudged Chandler, as he tried to use his body as a shield.

"Grow up, Chandler."

"You grow up."

"No, I mean _grow up_." Monica had succeeded into pushing him aside, Chandler was convinced she was stronger than any of the guys that picked on him in high school. She was now examining each of the items, stifling a laugh. "What's all this? Batman comics, Three Stooges figurines, Laurel & Hardy poster. That's the stuff you own?"

"This coming from a Muppet paraphernalia collector?"

Monica gaped in shock as her hand covered her mouth.

"Oh yeah, Ross told me," he added smugly.

"Fine," she said when her eye caught an item at the bottom of the box, while Chandler was picking up his stuff to put it back inside. "Is that a jewelry box?"

"It's―it's my grandmother's," he said, in a slightly panicked tone.

"That's … actually very sweet," she said softly and Chandler felt himself relax.

"Ok, what did you need me for?" she asked.

"Em, could I borrow some .. cooking things," he said, with mock gestures. "And stuff to sit on and sleep on." He shuffled his feet with his arms crossed.

"Where is your furniture?"

"I don't have it?"

"You don't own furniture? You're 23!"

"You're 22 and you own furniture! You're the freak here."

"Ugh, fine. You can sleep on my couch and have dinner with us," she went to open the door and turned to him. "Pottery Barn tomorrow, 6 a.m. Don't say a word to Phoebe."

"Thank you," he said with a grateful smile. "Oh and about the jewelry box―"

"Not a word to Ross. Got it."

A few days later, Chandler had furnished his apartment enough to make it slightly more welcoming: a clean, furnished home was nice but it was so quiet on his own, the place felt more like an echo chamber, he needed a roommate as soon as possible.

A kitchen table, bar stools, a sofa, and a bed made up his list of purchases― alongside a bunch of kitchen utensils he hardly knew how and what to use for but Monica had insisted on buying. The whole trip to Pottery Barn had been a succession of questions about the unexplainable functionality of some home goods―banana holders and mechanized egg crackers― to which Monica provided an extensive list of potential usages in highly improbable emergency scenarios.

He went back to her apartment and grabbed a beer from the fridge in what had become a daily ritual. There was no one in the living room, he spotted her silhouette on the balcony and joined her there. "What are you looking at?"

"Phoebe. She's helping her homeless friend, Lizzie, down the street."

Chandler followed her gaze, and indeed, there was Phoebe providing a homeless person with blankets and food. Monica's roommate was the most unpredictable and peculiar person he might have met in his life. How could someone who lost their mother to suicide, their step-dad to prison and lived on the streets be so cheerful and so … Phoebe?

"Isn't she amazing?" Monica sighed.

"That she is."

Chandler opened his beer, taking in the late summer breeze of the New York sky, sweeping his eyes between the buildings and the streetlights. His gaze landed on one of the windows from the building across the street.

"Is your neighbor … naked?" And is that underwear on the telephone pole? Oh, I love this neighborhood already!" He looked back at Monica who was furiously blushing. "Sorry, was that over the line?"

"No, no, I'm gonna go back inside―wait!" She sniffed him and frowned. "Did you smoke?"

"Y―yes" Chandler answered slowly. "In my apartment. By the window, are you going to call the police? I have witnesses!"

She glared at him and crossed her arms. "Chandler, you can't smoke in my apartment, or come in smelling all… smoky. Your choice."

"What about we make an arrangement, and I smoke once a week?" He bared his teeth, flashing a charming dimple but noticed Monica was unyielding. "Fine," he finished with a pout.

Chandler went back to his place and sat on the sofa. He picked out a cigarette from his pocket and examined it. Monica's apartment was nice, smelled nice and was inhabited by nice people. People who were willing to be his friends, even go as far as accept him just like he was, minus the smoking.

So he did what he always thought to be the best alternative when faced with a dilemma. A pros and cons list. If only he was at work, that spreadsheet software would prove to be really useful for once.

There were always plenty of reasons to stop smoking, but they never were convincing enough. Health reasons or simply limiting Ross's use of the air purifier. It still wasn't worth it―he didn't care that much about his health, and eventually, he got used to the humming of the air purifier. After a couple of months of cohabitation, it became white noise to him and he succeeded in ignoring it, like a soldier not getting spooked by the sound of gunfire in a warzone.

But Monica's apartment meant hanging out with Ross, Carol, Monica, and now Phoebe. Sure, he wasn't a fan of Ross and Carol's lovey-dovey displays, or Monica's nags and reprimands, and Phoebe was a mystery, but he had his own (and many) flaws. There was a chance they could all become friends―good friends, potentially best friends? He dared to hope.

He shot a quick look at his empty-decorated apartment. Truthfully he was sick of empty homes, sick of his empty life, sick of himself. Yes, friendship could be a worthwhile reason.

He thought about the reason he started smoking. His parents' terrible divorce― the pawn games, the neglect, the yelling and fighting. Those were good reasons to start smoking in his mind. For a 9 years-old lonely kid, it was an easy fix when his mother's packs of cigarettes were lying around, in plain sight and so easy to grab.

Good reason to start, but what about the reasons to keep smoking?

If someone asked him "Why do you smoke?", he couldn't come up with a good answer. He enjoyed it, he felt subconsciously it would make him relax whenever he felt nervous. There was something oddly comforting about the sound of the flame bursting from the lighter, caressing the tip of the cigarette, and the feeling of it between his fingers, savoring every nicotine gust. The morning cigarette, the one after a meal, the one at night roaming the dark streets, or the cigarette after sex―one he was yet to experience but imagined being the finest of them all.

The pros and cons list wasn't working. Maybe there was a compromise. Cigarettes were a coping mechanism, his way to deal with past trauma and feel just a little better about himself, but even he knew depending on it was surely not a good idea.

And now, with a job, an apartment, and friends, it was time to become more independent. Maybe he would never stop being a smoker until he dealt with all his issues, but for now, he could still stop smoking, go on a hiatus of some sorts.

Chandler put the cigarette back into the pack. That one gesture made him feel strangely empowered. He could stop smoking, he could achieve something, and it could make him feel good. His friends were worth it.

A week later, he settled on a new roommate, a guy in his mid-20s going by the name of Kaplan "Kip" Weinberg. He was the most convincing candidate from the few interviews Chandler conducted. He looked serious, had a steady job, promised to be clean, and Chandler had to admit, he was quite charming. He thought for a second he could possibly be a good wingman in case they hit it off and became good friends, but at worst, he would make for a decent roommate. A welcome change after four years contained in the same room as Ross.

He was a little taken aback when he introduced Kip to Monica, Phoebe, and Ross. The girls looked mesmerized, forcing Chandler to reexamine Kip. He was charming, sure. Reasonably tall, slightly taller than him, light brown hair, hazel eyes, chiseled jaw … The realization came to him then. Kip was definitely handsome, and if he ever was his wingman, Chandler would be the _funny guy_ at best.

He had no reason to hate him though or feel uncomfortable around him. He was nice and polite. Ross liked him; and the girls would get over their little crush, Chandler speculated. Monica could have any man she wanted, surely she wouldn't need to go across the hall to get a boyfriend, and Phoebe had already mentioned 3 dates she had over the last few weeks since they met, each one sounding crazier than the other: a guy in the navy, an ice-dancer, and a puppet guy—Kip would be too normal for her.

He had just moved from Philadelphia with few boxes and very little furniture. He worked as a gym instructor and had the body to show for it. In fact, one of the few furniture pieces he bought with him was a home gym equipment he placed in the corner of the living room.

Working out wasn't one of Chandler's hobbies but he was still delighted they got along well, Kip liked sports and watching mindless TV. He turned out to be clean, an early riser and very outgoing.

That night, after another dull day at work, Chandler went to Christopher's Pub and met down there with Monica, Phoebe, Kip, Ross and Carol sharing drinks and shooting pool, discussing their days and joking around. When he went to sleep, he couldn't help but feel a sense of belonging, of trust and understanding, a safe space where he could just be true to himself.

Usually, that feeling never lasted for too long.

The problem according to him, it was autumn. And just like Frank Sinatra sang, autumn in New York was often mingled by pain for Chandler.

He always had a sense of dread about this particular season. Thanksgiving was approaching, pumpkin smells were inescapable, it made him instinctively on guard.

In the morning, he heard voices and laughs coming from the living room. When he opened his bedroom door, he found Monica and Kip standing by the kitchen. Monica was holding a casserole, leftovers from dinner he suspected.

What he really saw and noticed though was sparks. Sparks flying everywhere, eye-blinding sparks. Kip was a talkative charming guy, and there he was, charming the hell out of his friend.

He joined them but was sure they hardly noticed him.

"It's funny that you work at a gym, I stopped going to one a few years ago but I was thinking about joining again," Monica said to Kip.

Chandler's eyebrows shot up, he had never witnessed Monica behaving this way before, trying so obviously to please and flirt with a guy.

"I thought you preferred outdoor runs?" said Chandler. They both suddenly turned to him, noticing him for the first time since he was in the living room.

"Oh Chandler, I didn't see you there," she told him.

"Being invisible is what I do best."

"Well Monica," said Kip, bringing the focus back to their gym talk. "If you want to join a gym, we'd be happy to have you. I work at the one on Tenth Avenue."

"Tenth Avenue? I know that place, I've been there!" Monica said. With way too much enthusiasm, Chandler reckoned.

"I'm not surprised, clearly you work out," Kip said, flashing a toothy grin.

"Oh well, you know, just trying to stay healthy."

Monica was blushing. Chandler couldn't believe it, he hadn't seen Monica Geller blush since Thanksgiving 1988―when she was a naive, overweight and impressionable teenager.

Kip was one smooth bastard.

* * *

"You two are perfect for each other!"

Chandler heard Phoebe exclaim the words to Monica in a fit of giggles and squeals, as he entered the girls' apartment.

"Me and Monica? That's what I keep telling her. Thank you, Phoebe."

Phoebe waved a hand at him. "You hush. This is important."

"Who's perfect for Monica?" he asked with dread.

"Kip. They're like the same person!"

Were they? It seemed Chandler was constantly reconsidering his first impression of Kip, he wondered why he didn't notice that during his interview.

"I'm not sure it's a good idea to date a friend who lives across the hall," Monica objected.

"I agree," Chandler added, almost on instinct which earned him a scolding look from Phoebe.

"Mon, he's not just a friend who lives across the hall, he's a _hot_ friend who lives across the hall," Phoebe argued.

"I am right here," Chandler deadpanned.

"He is pretty hot, isn't he?" Monica was blushing and smiling shyly.

Phoebe nodded. "I would have been all over that if you two weren't making googly eyes to each other since you met."

Googly eyes since they met? Chandler shook his head. How could he have missed all of that?

"We do have a lot in common," Monica added.

"Are you kidding? He loves running, he works out, he loves cooking and he's just so charming and mature. He's exactly your type."

"You know my type?"

"I know everybody's type. It's one of my many talents."

"What's Chandler's type?" Monica asked with a teasing smile.

"Oh, you don't want to know," Phoebe answered, with a dead serious look on her face. Monica shot an amused look to Chandler, then got up.

"All right. I like him a lot, I'll think about it."

Kip and Monica flirted for a couple of days after that, to his dismay. Chandler was often caught in the middle of their banter and glances. He was almost relieved when his roommate finally asked her out on a date, and in the least surprising turn of events since the outbreak of World War II, she had said yes.

Chandler did genuinely like Kip. He was effortlessly cool, organized, centered, and a great roommate. But he didn't feel at ease with him dating Monica. Not out of jealousy, but out of protectiveness. Kip was almost too cool, he didn't seem fazed or disturbed by anything, he had no demons or skeletons in his closet.

Ok, maybe he was a little jealous. Monica was the first real friend he made after Ross, and her nagging and obsessiveness were solely focused on him before Kip. And he liked the nagging, it felt strange, someone so willing to take care of him and focus so much attention on him. A pleasant novelty in his life.

Yes, part of it was this strange vibe about Kip, and the other part was about getting less time with one of his best friends. He felt uncomfortable being either the buffer or the third-wheel. The awkwardness reached new heights when Kip convinced him to buy a hibachi together for "barbecues on Monica's balcony" before admitting it was just a way to show off his knowledge about Japanese cuisine to her.

Kip was annoyingly tall and attractive to Chandler now. He tried, very hard to be okay with this blossoming '_love at first bite' _romance, but he still couldn't get rid of the niggling dread.

Or maybe, it was just Thanksgiving.

"I hate this stupid day," Chandler said, collapsing on the couch beside Phoebe and Ross, while Monica and Kip were sharing the armchair.

"That's the spirit," Kip commented.

"I hate traditional food. I hate football. I hate forced family time. I hate the stupid parade," he added. Ross and Monica turned their heads to him, raising their eyebrows teasingly. "Ok, the parade is okay, but I still hate Thanksgiving."

"What's with you and Thanksgiving―" Kip started but was immediately cut off by a chorus of groans from the others.

"Kip, honey, you just opened a can of worms," Monica said.

"Get this. I'm 9 years old, we're in the middle of Thanksgiving dinner―"

"Here we go," Ross grumbled.

Chandler ignored his friends and turned his attention to Kip and Phoebe. "And my parents with their impeccable timing, announce to me they're getting a divorce."

"That sucks, Chandler," Phoebe said, patting his arm. "You've got to get over this though, grudges are bad for your ethereal soul."

Chandler rolled his eyes. Kip got up and headed to the kitchen. "She's right, holding onto grudges like a badge of honor will hold you back in life, dude," he added.

"Impressive. Someone took Intro to Psych in college," Chandler rumbled under his breath. He watched Monica and Ross getting up, reaching for their coats and Kip trotting a suitcase, all of them waiting expectantly for him to finish his Thanksgiving moping.

The Gellers were going to their parents' house in Long Island, and Kip was visiting family in Philadelphia. Phoebe planned to spend Thanksgiving at the food kitchen, leaving Chandler the only one to boycott the holiday.

"I'll be fine. Go eat the merry food and give thanks to your functional non-divorced families. I rented Die Hard because I've only watched it 9 times this year," he said, waving at them. Monica stopped in her steps by the kitchen.

"Ok Chandler, your grilled cheese and your tomato soup are waiting for you, and there's some chicken in the fridge."

"Thanks, Mom."

Monica smiled, slightly bemused. "I'm leaving you the keys, I expect to find the apartment _exactly_ as I left it," she instructed.

"Ooh, I planned to rig the apartment with booby traps and leave the lights on to prevent burglars from breaking in."

Monica smirked at him as Ross opened the door, with Kip following suit. Phoebe stayed behind.

"You know Chandler, you do have a lot to be thankful for," she said after their friends left.

Chandler went to the fridge, bending and digging for beer. "For what? Friends with families to go home to, a hot roommate with the abs of Harrison Ford ...? "

"Those are nice abs," Phoebe gazed dreamily off in the distance, visibly entranced. "Nice to massage too," she continued with a beaming smile.

"You massaged Harrison Ford?"

"My clients' list is confidential."

Her expression was mock-serious. Chandler shook his head and took a sip out of his beer before going back to the couch.

"Look Chandler, I don't have a family either, but I have you, and I have Monica and Ross. They can be your family too," she paused, bending her head and lowering her voice."You're like the little brother I wish I had."

Chandler looked at her, surprised by her admission. "I am?"

"The annoying little brother I wish I had, absolutely."

He smiled at her and nodded gratefully.

"And if you're so jealous of Kip, maybe it's because you're not doing anything, you're not trying to go out and date girls."

"What are you suggesting?"

"I can set you up."

"Oh no," he said, feeling uncomfortable. "I don't do blind dates."

"Then it's not a blind date. I have her picture right here."

He was about to tell her it wouldn't be necessary when she reached for her oversized bag and picked up a picture from it, leaving Chandler speechless.

"Come on, give it a try. She's cute and she's fun, it's exactly what you need."

She was cute, he concluded after looking at the picture. Chandler rubbed his palms together. "Ok. Let's do that."

* * *

_Part 2 in the next chapter._


	2. Part Two

Chandler woke up with a throbbing headache. His eyes opened, staring mindlessly at the ceiling. He closed his eyes again until he realized it was definitely not the ceiling of his room.

He tried to see through the darkness and made a double take when he finally noticed something, or someone actually, stirring beside him, and his mind slowly put everything together.

It all came back to him in a rush.

The night before, the date set-up by Phoebe.

He remembered the awkwardness, the long silences, the utter lack of conversation and connection he had with the girl. And he remembered cutting the date short when she had said _supposebly_ instead of _supposedly, _multiple times, and he claimed a family emergency as a pretext to leave after a bathroom break.

But the woman beside him wasn't Miss_ Supposebly_.

He remembered getting an unexpected call from Gandalf―all of his friends had dates, Ross with Carol, Monica with Kip and Phoebe with her guy of the week. He succumbed to the temptation, and went to the ultimate NYU hangout bar: the Reservoir, famous for its cheap beer and flocked by college students on a budget.

Chandler looked at the woman beside him, they had sex and he had lost his virginity in the process. _Freaking finally_.

He thought this day would never come. There was little hope for a guy with the social skills expected of someone raised by a pack of wolves and whose teenage years were marked by an utter lack of interaction with the opposite sex.

In all fairness, it didn't feel as grandiose and glorious as his deepest wishes and dreams―there were noises and faces he wished he could take back. Noises and faces he wished she had made.

It was ok, it was _nice_. Bad sex was still better than no sex at all. But he was slightly disappointed it wasn't the earth-shattering, life-changing moment he thought it would be, and if X-rated movies were to be used as a reference, neither was it for her.

He got up and looked for his clothes. More details of the night before came back to him: she was a cute brunette, starting her senior year, either a med major or liberal arts major, going by the name of … Colleen Mosilla. Or Maureen Rosilla. He remembered quipping about her name when she quipped about his name, which led him to remember the reason she fell for for his charm and insisted on having sex on the basis of _'it's what you do in college'_― oh no.

"That's low. Even for you, Bing," Monica said crossly, looking at him from his refrigerator's door. He was recounting the events of the night to her.

"Hey! You don't know what it's like for guys like me out there. It's easy for you, you don't know the struggle," Chandler defended from his seat at the counter.

"She thought you were a Kennedy? How? I mean, why?"

"She was horny, I was horny, Gandalf introduced me as a Kennedy, I don't even know why. She believed it. I was sad and pathetic so I went with it."

"What a romantic story." She pulled her cheek up in a sarcastic smile. Chandler sighed, blinking down at the swirling white on his coffee.

"Chandler Agamemnon Bing!" Phoebe yelled, bursting into his apartment.

"What?"

Chandler and Monica looked stumped.

"What's your middle name?" Phoebe asked, in a calmer tone.

"W―Why...Why do you want to know my middle name?" Chandler mumbled.

"So I can middle name you when you do something bad! Like now!" She pointed her finger at him. "Why did you leave Judith at your date, last night?"

"Who's Judith?" asked Monica.

"The girl I set him up with."

"Wow. I underestimated you, Bing," Monica added, with a teasing smile.

"No no no. Phoebe, I'm sorry, but she was such a dud. She said _supposebly_," he said slowly for the sake of emphasis.

"So?"

"_Supposebly_. Are you kidding me?"

"You're a lost cause, I'll never set you up again."

"This is fun!" Monica exclaimed. "So you left a girl on a date and you ended up sleeping with a college girl that 'mistook' you for a Kennedy?" She shook her head, laughing.

"You did what?" Phoebe glared at Chandler.

"It just happened I swear, I didn't plan this. These things don't happen to me."

Chandler held his head in his hands. Phoebe's severe expression softened.

"So you scored last night? Ok, it's fine then."

He looked at her suspiciously, as she joined him at the counter and sat next to him, picking from the cereal box. "Tell me about this girl. Are you going to see her again? This is exciting!"

"Oh no. Never seeing her again. On my way out, I found a Yanni album in the living room."

* * *

The most wonderful time of the year, cheer and joy, decorated homes, angelic children looking forward to their gifts, happy couples, people surrounded by love and cared for by other wonderful people.

If there was a time to be naturally cynical and sarcastic for Chandler, it was Christmas time.

He tried really hard to find an excuse to mope around and jab about the holidays but things were changing. He did have friends, they were going to be exchanging gifts and spend time together. In fact, they were seeing each other pretty much every day.

He even let himself enjoy the delicious scents coming from apartment 20. Pine needle smell with sweet chocolate and freshly baked blueberry muffins. Monica had gone all out to make her place look like the holidays' window displays of a department store on Fifth Avenue.

A few days before Christmas, his mother had called. She was stopping by New York and had invited him for lunch with an announcement.

Chandler looked down at his plate, where only some beans and the bite of his enchiladas remained. They had talked for an hour or so, although it was more of a monologue at this point. His mother was reciting anecdotes from her travels and her books signings while Chandler kept nodding in response.

After a silent pause, Nora took a sip out of her glass of wine before carefully looking up at her son. "My publishers think I should go back to Nora Tyler Bing."

A hush fell over them for a second, before Chandler threw his napkin on the table.

He inhaled and glared at her. "What? I thought we were over that."

"I'm sorry, honey. For some reason, my books sell better when I'm Nora Tyler Bing. I need the _Bing _there, I don't why, there must be something about this name," she mused.

"This is your announcement? To ruin my life some more! Thank you, mom, what a great Christmas gift," he said, his tone dripping with anger and sarcasm.

"Chandler…"

"Why don't you just take a pen name?" He looked over the restaurant then said quietly, "Everyone will know my mother writes porn!"

"Erotic novels, Chandler."

"Whatever."

"I'm sorry, kid. There's no way around that, it's my career. Your father owes me that at the very least."

Chandler's eyes widened, his nostrils open. He chuckled nervously. "Oh God, it's always about you two, nothing has changed. What about me? There are 20 people named Bing and I'm one of them! "

"Chandler, stop being so embarrassed by your heritage. I am proud of who I am, I won't change my name."

Chandler stood up, reaching for his wallet and pulling out a couple of twenty dollar bills. "I'm going home. Merry Christmas, mom."

When he arrived in the hall of his apartment, Chandler went directly inside the girls' place. It was already filling up with coworkers, acquaintances, and friends, most of them he didn't know, but then he spotted Ross with Carol, Kip, Monica, Phoebe by the window and relaxed.

It wasn't so bad. The Christmas party looked great, the sweet Christmas music and the decorated lights, was enough to cheer him up.

His friends were there, he instantly felt better and safer with them, and looking at them from afar, he realized they were the most important relationships in his life―and if his friends were more his family than people he shared DNA with, then so be it.

After the New Year, Kip and Monica started spending every night together, most of them in Kip's room, which began to irk Chandler. He didn't want to hear them through the walls and frankly didn't expect their romance to take off so fast. He wondered if they developed genuine feelings for each other.

His initial worries about Kip dissipated, however, and unwanted noises aside, he was genuinely content two of his closest friends were in a happy relationship. Phoebe was right, they had a lot in common, they were both driven and energetic people. They went on runs together, they cooked together, they were almost in-sync. Chandler thought he could never live up to Monica's expectations of a boyfriend―if he exercised with her he would die trying to keep up, and if they cooked together she would kill him for ruining both the dish and the kitchen. They lived their lives at two extremely different strokes.

Not that the thought of dating her had entered his mind. It definitely never entered _her_ mind so there was no point into making up fantasies.

During one of their group nights hanging out at the bar, while Kip and Monica were playfully teasing each other by the pool table, Phoebe joined Chandler who was sitting at the counter, holding his glass with his fingers brushing away the drops of condensation.

"Did you hear? Isn't it great?" said Phoebe, leaning against the counter and looking at their two friends.

Not feeling in the mood to gossip, Chandler simply shook his head.

"Monica is thinking about asking Kip to move in with her!" she exclaimed.

His eyes went wide and he coughed as he swallowed his drink. "What? Why?"

"Oh no," she said in a deflated tone. "You _didn't_ hear."

"That's too soon! Isn't it too soon?" he paused, the implications slowly hitting him. "I won't have a roommate! Oh God, are you going to be my roommate?"

"You couldn't handle me as your roommate, Chandler Bing."

"I'm sorry. But that's crazy. She's being crazy, right?"

"It depends. Compared to what?"

Chandler raised his eyebrows as if to state the obvious. "Not you."

"Oh, then yeah." Phoebe nudged him and prompted him to look at the couple with a chin movement. "But they're really into each other," she sighed. "I love whirlwind romances."

"Yes, it's a real whirl of … wind." Chandler cringed, running his hand through the front of his hair. "I can't believe she didn't tell me," he said softly.

"Don't worry, Chandler. I'm sure she has good reasons for not telling you, probably to avoid you freaking out like you just did," she teased. "And if it happens, we won't be roommates. Actually, it's perfect timing because I'm thinking of moving out anyway."

"What?" Chandler coughed in shock for a second time. "What is happening around here? You're moving out? Why don't people tell me stuff?"

"Calm down. I love Monica, she's an amazing friend but she's an impossible roommate. She freaks out about one small crumb on the floor or flake of glitter in the bathroom," she said, in an increasingly panicked tone. "I can never live up to her expectations. I can't do it anymore, Chandler. I can't! I can't―"

"Ok, I get it." Chandler squeezed her shoulder. "Breathe."

Chandler _did_ get it. He was surprised at first that Phoebe and Monica had gotten along so well when they became roommates, but grew to believe it. After all, they were both kind and generous and fierce. He guessed living together was just a step too far for their otherwise clashing personalities. Lost in his thoughts, he took a gulp of his drink, draining it with a long swallow before looking up to Phoebe. "Please let her down gently? I know she's going to be sad and she'll think she's going to lose you."

"Of course." Phoebe nodded. "We'll still be friends. That's why I'm waiting for Kip and her to move in together."

Chandler looked again at Monica and Kip, he didn't understand why she didn't talk to him about her and Kip moving together. He felt apprehension building inside him. Phoebe moving out, Kip and Monica living together, Carol and Ross married―it was selfish but he didn't like all the changes happening just when he felt settled for the first time in his life.

* * *

Chandler was in a foul mood. He had been for weeks and he didn't know why exactly. Granted, he never was the cheerful kind, but what usually amused him just made him snippy now.

His grumpiness could only have been caused by the looming shadow of Valentine's Day or seasonal depression or work just being really, really dull.

What annoyed him most was probably the increasingly excessive public displays of affection from Monica and Kip. He started to think it wouldn't be so bad if they lived together in her apartment, so he could be in peace at his place. Most of the time, he felt invisible to them, having to block out the noise and try to focus on whatever was airing on TV.

It was unfair. He had found himself more and more reliant on them at exactly the moment that they had become less available to him. He just missed hanging out with each of them―when Monica would spend late Saturday nights with him, watching TV. They had become each other's support system. Monica was like a wizard. He'd give her a shirt with an old grease stain and she would get it out, he'd lose his keys and she would find them, he'd borrow out of her toolbox and kitchen utensils. She was a fixer, and he had been her newest, toughest project to date, that required all of her energy and attention.

He wasn't her fixer, but at least, something like a teddy bear, pretty useless for most stuff but there to provide emotional support. He'd be there after a depressing dinner with her parents or a bad date, it wasn't a lot but enough to make him feel good about himself.

And now she didn't need his comfort, and she was working her magic for Kip.

Kip wasn't exactly his closest friend, they were too different to hang out all the time but they worked well as roommates. The important thing was that, as the latest addition, he got along with their group. He was fully a part of it, and the group was _everything_.

The matters of the heart were not helping either. Ever since his failed blind date turned into fiasco first-time sex, he went into full hibernation mode―avoiding even the bar. It was too depressing, his life was empty before but maybe it was time to give up and fully embrace the emotional void and numbness.

He knew his friends were getting annoyed with him and his slouching, glued to his sofa in his sweats for hours.

Monica, in particular, was giving him the Geller death glare whenever she came back on a date with Kip and they were about to take things to the bedroom only to stop at the sight of him in his robe watching Law and Order in the living room.

One night, Phoebe and Monica came to his apartment and ambushed him, seemingly determined to get him out of his sweatpants-wearing phase.

"Don't you want to have sex with a woman?" Monica almost yelled.

"Yes, Chandler, what are you a monk now?" Phoebe added, then whispered to him, "Is everything working down there?"

"Hey! I could have sex if I wanted to," Chandler protested, with an outraged look on his face before he sighed. "Great, I sound like crazy Heckles now."

"Come on Chandler, you're cute, of course, you could have sex," Phoebe reassured.

"Cute doesn't get you sex," he mumbled.

Monica stood in front of the TV, Chandler tried to wave her off but she didn't yield. "Yes, cute doesn't get you sex, because to have sex you need to leave your damn couch, and go out!"

Chandler frowned with a stubborn expression. Monica knelt down to meet his eyes. "It's getting ridiculous. You're sweet and you're cute, and there are a lot of girls who would have sex with you!"

Chandler's eyes slowly widened, his left eyebrow arching significantly and a smirk appearing on his face.

"Not with me, doofus," Monica said.

"Yes, with someone more in your league," Phoebe chimed in.

"You two are doing wonders for my self-confidence." He finally stood up, and walked towards the fridge. "Of course I want sex. I'd like to have sex," he conceded, "but everything that comes with it isn't very appealing to me right now."

He took a beer and opened it, the girls followed him as he repositioned himself on the couch. "The flirting? The mind games? The small talk? The putting on of actual pants? No, thank you. These sweatpants and this couch are very comfortable."

"Ugh. I give up, Pheebs." Monica snapped, shooting looks at Chandler. "I'm going out with Kip, we're coming back here and I'm sleeping in his room tonight, so deal with it."

Monica left hastily and Chandler swallowed to stay composed. It was one of the few instances they were both being stubborn at the same time, and as far as Chandler could remember, it was never a good look on either of them.

Phoebe snapped him out of his thoughts. "What's the deal with you?"

"No deal," he defended, mindlessly drinking his beer and staring straight at the TV.

"You're grumpier than usual. Is it because of Kip? Or Monica?"

Chandler suddenly looked back at Phoebe with worried eyes.

"Oh, it's the both of them," she added.

"It's not like that! I just want to hang out with my friends," he said softly.

Phoebe's face softened. "Oh Chandler, you're not losing them."

"Feels like it," he said, in an almost whisper and staring down at his lap.

"Look Chandler, I don't know Kip that well, but I know Monica. She's not easy to get rid of, and God knows I've been trying!"

Chandler straightened himself. "About that, is there any chance you could reconsider?"

"I don't know, Chandler," Phoebe said, she looked at Chandler's pleading look. "Maybe ... I'll wait for the right time."

"I understand."

She nudged him to sit beside him on the couch. "Listen, they won't stop being your friends."

"That's what everybody says."

"I have a good sense about things, and I sense that Ross and Monica won't ever leave you, mostly because, let's be fair, you're their closest friend, and you and I both know it's not easy for anybody else to tolerate them," Phoebe joked, making him smile.

"You'll always be their number one friend, even if Monica is dating Kip," she paused, weighing her words. "For now."

"For now?"

"I can't disclose everything I sense, Bing. I don't want to mess with the natural order of the universe."

Chandler nodded. "Of course."

"But I can disclose that you're going to be fine," she said, ruffling his hair.

The next day at work, Chandler was sipping his coffee at his desk and opened a spreadsheet, ready to input numbers and find a distraction to waste time, he thought again about his friends' plea for him to 'go out and have sex'.

He looked at the chart on the computer, generated by the weekly statistics net usage, and an idea popped into his head.

He opened a new spreadsheet and created a new chart. The _x_ axis displaying the years between 1985 and 1991. On the left side, the _y_ axis listed number of dates/people, it went from zero to five. At the top of the chart, Chandler hesitated a second before typing the title: _My love life_.

Chandler never developed the vocabulary necessary to express or understand the many colors and intricacies of adult emotions. All he had, from watching and listening to the adults around him, was a language for negativity, and people sensed that and he realized early on he was headed for serious trouble in life.

He figured reducing the complicated tortuous mess that relationships were to numbers would allow him to understand them, and solve the mystery of his miserable dating life.

The chart generated indicated that the numbers weren't exactly flattering.

In high school, he could get away with the excuse it was an all-male boarding school and consequently, the opportunities were rather limited. Still, there was his first girlfriend, Julie Grath, whom he met in summer camp. He did break up with her because … well, because, the third summer she got fat.

There was Missy Goldberg in college, which involved some interesting make out sessions in the science lab, but guilt had caught up with him. Ross also liked her and they had made a shaky, questionable 'pact' not to date girls they both liked.

He almost forgot about Dana Keystone in college. One date, one very dull date.

In more recent times, there was the girl he lost his virginity to, Maureen Rosilla. It pretty much was a one-time thing, since she never asked about him again, and he couldn't get over her love for Yanni.

Finally, there was Phoebe's "supposebly" friend.

His train of thoughts was interrupted by a realization. There was a trend there. He was always the one to pull the trigger on these relationships, he was the culprit, responsible for his own ache and misery.

When he went home that day, he asked Phoebe to get him another date with Judith. He decided to give it another chance.

It turned out they really didn't connect at all, and this time, he knew it would never work out, not just for grammatical differences.

Chandler liked to think it was, nevertheless, progress. He was out there and he would give the girls interested in him more than one date. Of course, in an ideal world, the girls interested in him would coincidently be the girls he was interested in.

He went on a few dates after that, and although it didn't prove to be fruitful, it made him feel better about himself, and his prospects.

He didn't hear anything again about Kip and Monica moving together and he had actively avoided the subject in their company. It was for the better. Things had settled, their group found a routine; even if to Chandler, it was a fragile one, with Phoebe still thinking about moving out.

When Valentine's Day came, Chandler was surprisingly upbeat. All his friends went on dates, but for once, he wasn't going to pity himself and stay home in his robe watching TV. He decided to go out with his coworkers. Work was dull, but people liked him at his job, and he enjoyed hanging out with them.

When he woke up the next day, he felt his head pleasantly light, he came home not too late, not too early and drank just the right amount. It was a Saturday, and he was impatient to hang out with his friends. When he came out of the room, he found Kip in his pajamas, with no sign of Monica in the apartment.

"How was your Valentine's dinner with Monica?" he asked Kip.

His roommate held his head in his hand, shutting his eyes close. "Oh man, I officially hate Valentine's Day."

Chandler's ears perked up as he looked intently at Kip, waiting for him to elaborate.

"We started to talk about childhoods and high school, she wanted to know what was it like being the quarterback of the football team and all that." He swallowed an aspirin with a glass of water before continuing, "And then she started talking about her childhood and crying and everyone was staring at us—"

"What? Don't ask her about her childhood, that's like making her watch Old Yeller on the plane! Floodgates. Open!" Chandler exclaimed.

"I was just making conversation, I don't want to listen to sad childhood stories on a date," Kip groaned, still holding his head. "It was a bad date."

"You should check on her," Chandler said coyly.

"Yeah, about that. Look, she's a nice girl but I don't think it's going to work out in the long run. I thought we were having fun, you know. Nothing serious."

Chandler tensed. "What? You were crazy about her, weren't you?"

"I was. I swear I was. I just … It's too soon for me to settle down, you know?"

Chandler shook his head, not quite believing what he just heard. After a moment of silence that felt like the tense beginning of a chess match, his roommate spoke again. "Look, she's great and I know she's your friend. I won't lead her on."

He didn't answer right away, feeling animosity twisting hotly inside him. "I see," he said dryly, then cleared his throat. "Ok. Be upfront with her. That's all I'm asking," he finished and with that, he left the apartment without another word.

Chandler entered apartment 20, he noted Monica's absence and felt an anxious leap in his stomach. He went out to run some errands before heading to the bar in the afternoon. There was, again, no sign of Monica. Kip was still standoffish about what had gone down the night before, and so Chandler decided to let it go.

When he went back to the apartment in the evening, he retrieved his mail and headed to his place. He put the TV guide destined to 'Miss Chanandler Bong' on the counter and mindlessly walked to the apartment across the hall. Just as he was browsing through the rest of the mail while opening the door, he found a letter addressed to him and signed _Charles Bing_.

Chandler froze. His knees went weak and he stumbled, almost tripping.

His father had tried to call and sent letters ever since he left for college, but this was the first time in months he reached out to him. He thought his dad had definitely turned the page, moved on from him once and for all. He almost wished it. It would be easier to deal with that, grieve and accept it rather than risk opening Pandora's box his relationship with him had always been.

Chandler studied the letter for a while longer, it was his father. Of course, he still cared about him, despite the bitterness, despite the hurt, despite everything. He inhaled and started to open slowly the envelope.

"Chandler, is that you?"

He was interrupted by a muffled voice coming from the bathroom, tearing out his attention from the letter. Monica appeared in the living room. She didn't look good.

"Mon, what's wrong?"

"Nothing," she said, her voice small as she went over to the couch and lay down with a blanket. He had rarely seen her so dejected.

"Come on, you're not okay. Are you crying?"

"I―I'm not … It's nothing," she said, her sob ripping through as she hiccuped. "There's dinner and beers in the fridge if that's what you're looking for."

Chandler looked at the letter, then back at his friend. He went to the kitchen and threw out all the mail in the trash can, before heading to the couch. He kneeled in front of Monica who hid her face under the blanket.

"Oh Mon, you can tell me," Chandler said, lowering his voice. "Please?"

Monica slowly pulled out the blanket and wiped her tears away. "Kip doesn't want anything serious. He said that, last night … on Valentine's Day."

"Right." Chandler reached out to her with his hands, and held her as she was breaking.

"I'm an idiot," she said, pressing her face to his neck.

"No, you're not."

"I thought he liked me. How was I so blind? I'm an idiot."

Chandler tightened his arms around her. "Listen to me, Mon. You're not. He's the idiot."

"He's your friend."

"So? You're my friend too."

"How did I not see it coming, Chandler?" Another sob broke her voice on the last word. "He said it was too early for me to meet his mother, he said it was too early to think about living together and I ignored all the signs."

"It's not your fault."

"I feel so embarrassed. I told him I loved him .. last night, and he said he wasn't there. He didn't even say he wasn't there _yet_, he just said he didn't feel the same. He doesn't love me."

"He's an idiot, Mon, ok? You don't have to be embarrassed. You did nothing wrong."

Her tears subsided, forcing herself to smile at him and swallowing hard to regain composure. "Please don't say anything to Ross? I don't want to make a mess."

"I won't, but Kip's going to hear from me."

"Chandler, I don't want you to fight him for me. He just doesn't feel the same, I can't force him to. He was being honest."

"Still. This is no way to treat a friend, or a girlfriend."

He squeezed her hand and she looked up at him. Her tight expression relaxed into a shy smile. "That's sweet," she said, trying to breathe in and out to gather herself. "Was your Valentine's Day as bad as mine?"

Chandler shrugged and slid next to her on the couch. "It was all right."

Monica nodded, he could still feel her ache as she rested her head on his shoulder.

"You know what? Let's get those beers, and ice-cream, let's watch Pretty Woman!" he said, in an attempt to cheer her up.

"I don't have Pretty Woman."

"Well, I do."

Her eyes went wide, and she repressed a laugh. Chandler smiled, relief washing over him. "See, you're already feeling better."

Two hours later, the movie came to an end. Empty beer bottles were scattered on the table, with no coasters, which made Chandler realize they were both way too drunk. In a sober state, Monica would have freaked out already, and he would be too scared to even consider leaving bottle caps strewed around.

Instead, Chandler was still making jokes about the movie, mocking the shopping trips and the montages, both of them couldn't stop laughing.

Until, in a sudden change of tone, Monica said in a soft voice, "Have you ever told someone you loved them and they didn't say anything back, Chandler?"

"You don't want to open that door," he joked, and she nudged him, prompting to answer seriously. "I had a couple of 'oh, crap', once a girl told me 'so?', and another one said 'oh I have to go now' and she just left, in the middle of a date."

Monica gaped at him from over the top of her beer. "You made that last one up!"

"I wish," he answered despondently.

After another moment of silence, she turned to him and said, "The underwear on the telephone pole is mine, from the time I had sex with Bobby on the balcony."

"The underwear on―What? Yours? Oh my God!"

Chandler felt his own jaw creak open. Monica was casually cleaning water rings marks on the table.

"I need another drink, why is this stupid bottle empty," she said.

"No, no, back to the sex on the balcony story!"

"I think I'm drunk."

"But why?"

Monica cleared her throat and forced herself to look at him. "I don't know, it's pathetic, I was trying to impress Bobby, you know? I wanted him to think I was fun or something."

"Sex on the balcony, huh? Sounds kind of hot."

"Embarrassing myself is a running theme in my love life."

"Come on, Monica, it's not embarrassing! Look, when you meet the right guy, you won't have to impress him and he will love you back. These guys just aren't right for you."

Chandler put a gentle hand on her shoulder, and he finally felt her relax.

"Maybe you're right," she said, before shaking her head. "I can't believe I just said that to you. No one knows, not even Phoebe."

They were silent for a moment until she spoke again, almost startled. "No, you have to tell me an embarrassing secret!"

"Why? I won't tell anyone!"

"Obviously you won't, I would have to kill you if you do," she said with a smirk, "no one can know about this. But the balance in our friendship needs to be restored, so you have to tell me a secret."

"Balance? Secret?" Chandler swallowed back with a strangled laugh. "I don't have embarrassing secrets."

Monica looked expectantly at him.

"I don't!"

"Really Chandler? A guy like you?"

"Thanks," he said, deadpan all the way.

"We can't hang out together again with this one thing hovering over me. I can't even look at you anymore," she said in a hyper-innocent voice and a pout.

"Fine, fine." Chandler brought her hand and slowly shifted it over his chest.

"Bing what are you doing, I'm not that drunk―Wait, what is _that_?"

"It's a little bump," Chandler said in a small voice.

"A bump?"

"It's a third nipple, okay? I have a third nipple. Here, friendship balance restored!" he said in a burst of exasperation.

She laughed so loudly she snorted. "Oh wow. Balance very much restored indeed!"

"Don't be so giddy."

He hooked his arm through hers. "Let's just be two very embarrassed and lonely friends now." He smiled down at her, and after a couple of minutes, she dozed off on his shoulder.

* * *

Chandler Bing liked the spring.

It was still cold in New York by April, and in Manhattan, the buildings and skyscrapers were hiding the shy sun all day, but when he was back from work, and walking in the Village, parks were filled with strollers and blooming flowers. The late winter snow started to melt as the spring was announcing itself in the city.

He was in a good mood when he got home. He hadn't talked to Kip, aside from exchanging pleasantries, since Valentine's Day―he figured it wasn't his place to come between his two friends, and he shuddered at the idea of confronting him about it. The awkwardness that settled between the two roommates wasn't ideal. Kip stopped hanging out as much with the rest of the group, or vice versa, he couldn't tell. Chandler figured Monica had kept Ross and Phoebe in the dark about the 'time out' in her relationship with Kip.

His roommate wasn't home that night, which became a feature of the last few weeks. He'd come home late or even until the morning after.

Chandler dropped his keys on the counter when he noticed a package awaiting him. It was addressed to him, from his mom. He opened it to find 3 book copies of _His_ _Sweet Darkness _written by Nora Tyler Bing. He sighed and read the card accompanying it. "This is for you and for your friends, if you're not too embarrassed. Please read the dedication. Love you, Mom."

He turned the first few pages to find the dedication.

_To my son,_

_No matter how near or far apart we may be, remember I will always be there if you need me._

Chandler exhaled and sat on his couch, browsing briefly through the book. He couldn't help the embarrassment, it was almost a pavlovian response he had to his mother's extravagance. Her job, which was tied inevitably to her personality, made it hard on him growing up. His friends, and Ross, in particular, were always so in awe with his mother, her flamboyance and her oozing charisma, but to a kid, it was the ultimate nightmare―as she had slowly become more and more famous, her books were being read by other kids at school. It was hard enough dealing with his father coming out and leaving, his mother getting recognized for her sex knowledge didn't help either.

Why couldn't any of his parents just be … normal?

There were the condoms as gifts, the Playboy magazines lying around in the house, the lavish parties and the parade of men she dated; the unsolicited sex advice―and yes, he envied the kids that would be told a cute story when they asked where babies came from. Was is it so wrong he'd rather be sheltered than his mother believing open talks about sex was the right way to raise a kid?

Then send him out to a boarding school to 'prepare him for the realities of life'? He didn't feel he was raised to be independent, it felt to him like he was an inconvenience to her lifestyle. To both his parents' lifestyle.

Ironically, a liberating education without sexual taboos resulted in him feeling emotionally stunted and repressed. Humor and smoking were how he coped with the divorce, but before that, shutting down his emotions and feelings was the only way not to burst from embarrassment and anger―of living in an environment he hated, of his own parents forgetting he was kid or being blind to the damage that kind of exposure would have on him.

He looked again at the words she dedicated to him. Maybe he was being unfair. She did things her own way and she thought it was the right way. He wasn't sure he could blame her for being the way he was, as tempting an excuse it was, and it wasn't like he turned out to be so bad, just not manly enough, incompetent with women, afraid of change and confrontations―all parents mess up their kids to some degree. What he truly regretted was the lack of affection and attention. It seemed pretty mandatory to parenting and he would never understand why he was deprived of that.

Chandler loved his mother, and he didn't want to cut her out of his life. She didn't completely abandon him or forget about him.

He hoped one day he could muster the courage to have a real open conversation with her and tell her all these things.

One day.

For now, he picked up the phone, and left her a message to thank her for the books.

He went downstairs to the bar, Monica was at the counter, she smiled when she saw him. He liked knowing some people were happy to see him.

"Chris, two beers, please. And leave the bottle," she told the manager.

"Ah, sounds just like Christmas morning," Chandler quipped.

She laughed and nudged him, and Chandler was relieved their friendship was strong as ever. There was a comfort in that. No matter what happened: Accidentally severed appendages, late night drunk secret reveals or heartbreaks, they would still be friends.

"So, I'm back with Kip. I know what you're going to say."

He couldn't help but be surprised at the news, but there was a defeated look on her face.

"We're doing the casual dating thing," she added before he could respond.

"You don't do casual, Mon."

"No, I don't."

He tapped his fingers on the counter before looking at her and asking cautiously, "Are you giving it a try because you think he's the one or something?"

"Oh no no. He's definitely not the one."

"How do you know?"

"Because I just know. When it's _the one_, it's not supposed to be this hard."

Chandler smiled and raised his beer, clinking it with hers. "Not that I know anything about love, but that sounds good."

He took a sip and licked his lips. "And listen, whatever happens with him, you can talk to me. I mean, we're best friends, right?"

"Definitely."

"Yeah. Maybe."

"No, Chandler. _Definitely_."

His mouth curved into a smile and she beamed at him.

A few moments later, Kip appeared at the door of the bar, Monica said goodbye and joined him. Chandler watched them as they left. Casual dating definitely wasn't her thing, and he couldn't understand why she would keep dating a guy who didn't deserve her, but he trusted her to know what was best for her. Although sometimes he wondered if she knew what was best for everybody else but herself.

"You don't like Kip."

Chandler was startled and turned to find Phoebe behind him. He looked around to see how she got there, and typically, she didn't explain herself.

"I'm not exactly president of his fan club right now."

"It won't last."

He tilted his head and nodded. "I think so too."

"Chandler Bing, are you growing facial hair?" Phoebe got closer and studied his face.

"How did you know?"

"I sense things, remember! So I'm right, is it a mustache or a goatee?"

"It's time for a change. Goatee season is in full bloom with the kids so I thought why not. Maybe it would magically make me irresistible," he said, waggling his eyebrows.

"Oh, like Weird Al Yankovic!"

Chandler stared at her blankly. "_Sure_, Pheebs."

They were soon joined by Ross, who came alone that night, and Phoebe later left to visit her grandmother.

"Where's Carol?" he asked him.

"She didn't feel like going out. She hasn't been feeling like going out for the last few weeks," Ross replied.

"I'm sure she's just tired, man."

"Yeah." Ross took a deep breath before looking straight at him. "I guess you heard about Kip and Monica?"

"I did."

Chandler could read the concern in Ross's face.

"Do I need to worry about her, Chandler? You would tell me if there's something wrong, right?"

"Ross, Monica is a big girl, she can take care of herself."

"I know she does. But Kip has been distant and she didn't say much about them, he was supposed to meet our parents."

Chandler shrugged and patted his shoulder.

"I will always worry about Monica, I'm her brother," Ross continued, "but it makes me feel better to know you're keeping an eye on her. You know, just making sure she's doing ok."

Chandler laughed. "Ross, more often than not she's the one taking care of me, you know that."

"Yes, but I trust _you_. I like Kip, but you're my best friend and you know her better than any of us."

"Thanks, man," he answered with earnest gratitude. It did make him feel good to be trusted. Ross and Monica considered him their best friend and he couldn't help but smile at that thought.

* * *

When Gandalf called him to invite him to his latest graduation party, Chandler reminisced how terrified he was of life, in general, a year ago. How directionless and hopeless he was.

He still felt hopeless and a bunch of other things, but he had a job, an apartment and pretty great friends.

One morning, he walked into his boss' office and was offered a substantial raise. It turned out he was good at his job, and although he would never openly admit it, it sure felt nice to be good at something, even if it wasn't the most glamorous occupation.

So maybe this whole adult thing wasn't too bad. When he came home that night, he dropped his keys and suitcase and went into apartment 20, he found Phoebe and Ross sitting on the couch in a heated debate over an episode of Unsolved Mysteries; while Monica was busy adjusting new curtains over the balcony window.

They didn't need to hang out with him, they weren't obligated to give him their love and affection, or have to have him in their life. They chose to. He knew he'd freely give them his affection and work hard to deserve theirs.

He could go out to a bar any night of the week and hope to find a girl willing to sleep with him, and in reality, it wouldn't be that hard. But meeting friends, building solid friendships was no easy feat once people weren't confined to hang out together because they went to the same school and had to see each other every day.

Those friendships were rare and hard but felt easy and natural. They were the cure to that shock he felt a year ago, the feeling of loneliness and inevitable isolation fresh out of college.

The fact that Kip wasn't hanging out with them anymore, that he phased them out or he got phased out, willingly or unintentionally didn't really matter. It couldn't matter.

If there was one thing he realized about Monica, Phoebe and Ross, it was that being friends with them was a choice, a commitment but never a chore or a coincidence. They were fiercely loyal, if that meant being overprotective over each other and only accepted people who were willing to put the same kind of effort into their friendship, then so be it. He wouldn't change a thing about them.

Of course, if Kip decided to move out or leave, he could live on his own now thanks to his new salary. He felt capable of doing it, as long as he had Monica and Phoebe across the hall to keep him in line. Or he could get another roommate, a roommate who would enjoy the same things, who would become a true ride-or-die friend, a roommate Monica or Phoebe wouldn't have a crush on.

He was still not sure how this adulting thing worked, but Chandler Bing knew he was going to be okay.

* * *

**AUTHOR'S NOTE**

* * *

If you read all the way through this ridiculously long story, I'm so sorry and thank you!

I wish I had an excuse for this mess but I don't. Not really. I know what you're thinking: Haven't you heard of editing? Well, like the kids say: _editing? I don't know her._

I just had way too much fun writing all of this (and more) for multiple months (because I'm a crazy person).

**Thanks for reading, as always. Don't be afraid to leave a review to tell me you gave up halfway through :)**


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